Nestled in the Western part of Massachusetts, Berkshire County is brimming with cultural attractions, natural beauty, and quintessential New England charm. Whether you’re an art enthusiast, an outdoor adventurer, or someone who appreciates quaint towns and gourmet dining, the Berkshires offer a plethora of activities. Here’s a curated guide to some of the best things to do in this picturesque region.

Cultural Attractions

The Clark Art Institute

Experience world-class art nestled in the mountainous landscape of Williamstown at The Clark Art Institute. Housing a stunning collection of European and American paintings, sculpture, and decorative arts, it’s an art lover’s sanctuary.

MASS MoCA

A visit to the Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams is a must. This venue’s expansive galleries host large-scale, and often interactive, contemporary art exhibits that are as unique as the repurposed factory setting they inhabit.

Tanglewood Music Center

Indulge in the sounds of the Boston Symphony Orchestra at their summer home in Lenox. Tanglewood Music Center hosts classical concerts in an open-air venue, offering the perfect soundtrack for a summer evening in the Berkshires.

Shakespeare & Company

Enjoy world-renowned theater productions amid Lenox’s serene ambiance. With a focus on the works of The Bard, Shakespeare & Company delivers engrossing performances that keep audiences coming back.

Outdoor Adventures

The Appalachian Trail

For hiking enthusiasts, access to the Appalachian Trail is a dream come true. Whether it’s a day hike or a longer expedition, the trail offers a pristine wilderness experience.

Berkshire Botanical Garden

Explore the vibrant and beautifully maintained gardens at the Berkshire Botanical Garden in Stockbridge. The collections display a diverse range of flora native to the region and offer a tranquil retreat for visitors.

Jiminy Peak Mountain Resort

Adventure awaits at Jiminy Peak Mountain Resort, which provides year-round fun. In winter, it’s a ski paradise, while the warmer months offer Mountain Coaster rides, aerial adventure parks, and scenic chairlift views.

Paddle on the Housatonic River

Enjoy a peaceful day paddling down the Housatonic River. Whether by kayak or canoe, this river’s gentle flow and rich scenery make it perfect for family outings or solitary reflection.

Gourmet Experiences

5ive Steakhouse at the Wyndhurst Manor

This fine-dining steakhouse in Lenox offers a sophisticated menu with panoramic views. From the perfectly cooked prime cuts to the delectable sides, 5ive Steakhouse provides a memorable culinary experience.

Berkshire Mountain Bakery

Visit Berkshire Mountain Bakery in Housatonic, known for its naturally fermented, handcrafted bread. The bakery offers a variety of artisanal baked goods that are a true treat for the taste buds.

West Stockbridge Farmers Market

Explore the West Stockbridge Farmers Market for fresh produce, artisanal cheeses, and locally-made crafts. It’s the perfect spot to pick up picnic supplies or gifts.

Arts and History

Norman Rockwell Museum

Step into the world of beloved American illustrator Norman Rockwell in Stockbridge. The museum features the largest collection of original Rockwell art, including his best-known paintings and studio

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